An organophotocatalyzed C(sp2)-H/N-H cross-dehydrogenative coupling of cyclic aldimines with aliphatic amines has been disclosed, which represents the first example for visiable-light-induced C-H amination of N-sulfonylated imines. This methodology enables the...
All reactions were carried out in solvents dried using a Solvent Purification System (SPS). Thin layer chromatography was carried out using TLC aluminum sheets coated with 0.2 mm of silica gel (Merck Gf234). Chromatographic purifications were carried out using flash grade silica gel (SDS Chromatogel 60 ACC, 40-60 µm). NMR spectra were recorded at 23 º C on Bruker Avance 300, 400 or 500 Ultrashield apparatus. Mass spectra were recorded on a Waters LCT Premier Spectrometer (ESI and APCI) or on an Autoflex Broker Daltonics (MALDI and LDI).
Procedure for the preparation of products 2a-s and 4a-j.Representative procedure: To a solution of 1a (1 mmol) and 2-Cl-pyridine N-oxide (2.1 mmol) in CH 3 CN (5 mL) was added Hg(OTf) 2 (0.1 mmol) and the mixture was stirred at 23 C for 3 h. The solvent was evaporated and the residue was purified by flash column chromatography (hexane/EtOAc 20:1) to give the product 2a in 95% yield.
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